HUT77653A - Baktérium- és vírusellenes hatású N-szubsztituált 2-tio- és 2,2'-ditio-biszbenzamid- és -piridinkarboxamid-származékok és az ezeket tartalmazó gyógyszerkészítmények - Google Patents
Baktérium- és vírusellenes hatású N-szubsztituált 2-tio- és 2,2'-ditio-biszbenzamid- és -piridinkarboxamid-származékok és az ezeket tartalmazó gyógyszerkészítmények Download PDFInfo
- Publication number
- HUT77653A HUT77653A HU9700349A HU9700349A HUT77653A HU T77653 A HUT77653 A HU T77653A HU 9700349 A HU9700349 A HU 9700349A HU 9700349 A HU9700349 A HU 9700349A HU T77653 A HUT77653 A HU T77653A
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- bis
- methyl
- dithiobis
- acid
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 10
- 239000003443 antiviral agent Substances 0.000 title abstract description 8
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 6
- OEEHSSKRJOGQMP-UHFFFAOYSA-N 2-[(2-carbamoylphenyl)disulfanyl]benzamide Chemical compound NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(N)=O OEEHSSKRJOGQMP-UHFFFAOYSA-N 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 401
- -1 hydroxy, nitro, cyano, phenyl Chemical group 0.000 claims description 158
- 239000000203 mixture Substances 0.000 claims description 94
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 35
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 33
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 31
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- OTYIADUBGFZFSV-UHFFFAOYSA-N n-[4-(acetylsulfamoyl)phenyl]-2-[[2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]phenyl]disulfanyl]benzamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(S(=O)(=O)NC(C)=O)C=C1 OTYIADUBGFZFSV-UHFFFAOYSA-N 0.000 claims description 20
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 7
- 229960003767 alanine Drugs 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 6
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229960000310 isoleucine Drugs 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- ZTVZLYBCZNMWCF-UHFFFAOYSA-N homocystine Chemical compound [O-]C(=O)C([NH3+])CCSSCCC([NH3+])C([O-])=O ZTVZLYBCZNMWCF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229930182844 L-isoleucine Natural products 0.000 claims description 3
- IRWATDVXASEANM-UHFFFAOYSA-N [2-[(2-benzoylphenyl)disulfanyl]phenyl]-phenylmethanone Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 IRWATDVXASEANM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000000107 disulfanyl group Chemical group [*]SS[H] 0.000 claims description 3
- 229960001153 serine Drugs 0.000 claims description 3
- VGKOQKWTEXPMMH-UHFFFAOYSA-N 3-[[2-[[2-(2-carboxyethylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]propanoic acid Chemical compound OC(=O)CCNC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NCCC(O)=O VGKOQKWTEXPMMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- IURAMYCAJMCTKF-VYRBHSGPSA-N C(=O)(O)C(CCC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)N[C@H](C(=O)O)CCC(=O)O)C=CC=C1 Chemical compound C(=O)(O)C(CCC(=O)O)NC(=O)C1=C(C=CC=C1)SSC1=C(C(=O)N[C@H](C(=O)O)CCC(=O)O)C=CC=C1 IURAMYCAJMCTKF-VYRBHSGPSA-N 0.000 claims description 2
- BIRDLPVUVRPQQZ-XJDOXCRVSA-N CC1=C(C(=CC=C1)SSC2=CC=CC(=C2C(=O)NC(CC(C)C)C(=O)O)C)C(=O)N[C@@H](CC(C)C)C(=O)O Chemical compound CC1=C(C(=CC=C1)SSC2=CC=CC(=C2C(=O)NC(CC(C)C)C(=O)O)C)C(=O)N[C@@H](CC(C)C)C(=O)O BIRDLPVUVRPQQZ-XJDOXCRVSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 2
- 235000014852 L-arginine Nutrition 0.000 claims description 2
- 229930064664 L-arginine Natural products 0.000 claims description 2
- VSPDOHZYXSHFNN-UHFFFAOYSA-N N-(2-morpholin-4-ylethyl)-2-[[2-(2-morpholin-4-ylethylcarbamoyl)phenyl]disulfanyl]benzamide Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)C(=O)NCCN2CCOCC2)C=1C(=O)NCCN1CCOCC1 VSPDOHZYXSHFNN-UHFFFAOYSA-N 0.000 claims description 2
- AXAMDLXRGAOKNH-UHFFFAOYSA-N [2-[[2-(pyrrolidine-1-carbonyl)phenyl]disulfanyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=CC=C(SSC=2C(=CC=CC=2)C(=O)N2CCCC2)C=1C(=O)N1CCCC1 AXAMDLXRGAOKNH-UHFFFAOYSA-N 0.000 claims description 2
- 229960000250 adipic acid Drugs 0.000 claims description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- BYVOQRXIYBJYQJ-UHFFFAOYSA-N n-(2-propan-2-ylphenyl)-2-[[2-[(2-propan-2-ylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound CC(C)C1=CC=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(C)C BYVOQRXIYBJYQJ-UHFFFAOYSA-N 0.000 claims description 2
- VNHUWYHGLHKLKH-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-[[2-[(3,4-dichlorophenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(Cl)C(Cl)=C1 VNHUWYHGLHKLKH-UHFFFAOYSA-N 0.000 claims description 2
- KRNWWEIKCXPQDA-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)C=2C=CC=CC=2)=C1 KRNWWEIKCXPQDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 239000003279 phenylacetic acid Substances 0.000 claims description 2
- HITDPFLPATVPPI-UHFFFAOYSA-N tert-butyl 4-[[2-[[2-[[4-[(2-methylpropan-2-yl)oxy]-4-oxobutyl]carbamoyl]phenyl]disulfanyl]benzoyl]amino]butanoate Chemical compound CC(C)(C)OC(=O)CCCNC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NCCCC(=O)OC(C)(C)C HITDPFLPATVPPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- JKUQJDKTSHFABM-UHFFFAOYSA-N 3-methyl-n-(4-sulfamoylphenyl)benzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=CC(=CC=2)S(N)(=O)=O)=C1 JKUQJDKTSHFABM-UHFFFAOYSA-N 0.000 claims 1
- CCIQAXMAJRUSBB-UHFFFAOYSA-N 4-[[2-[[2-(3-carboxypropylcarbamoyl)phenyl]disulfanyl]benzoyl]amino]butanoic acid Chemical compound OC(=O)CCCNC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NCCCC(O)=O CCIQAXMAJRUSBB-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical group CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 1
- KSOXWUWHJAZNDP-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-2-[[2-[(2,4-dichlorophenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(Cl)C=C1Cl KSOXWUWHJAZNDP-UHFFFAOYSA-N 0.000 claims 1
- YYMXLCAYSGEQOW-UHFFFAOYSA-N n-(4-carbamoylphenyl)-2-[[2-[(4-carbamoylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=C(C(N)=O)C=C1 YYMXLCAYSGEQOW-UHFFFAOYSA-N 0.000 claims 1
- KPPIPRMPXLCHFE-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[[2-[2-(dimethylamino)ethylcarbamoyl]phenyl]disulfanyl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NCCN(C)C KPPIPRMPXLCHFE-UHFFFAOYSA-N 0.000 claims 1
- CXHMSESVHOAWJC-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-2-[[2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]phenyl]disulfanyl]benzamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)C=2C(=CC=CC=2)SSC=2C(=CC=CC=2)C(=O)NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 CXHMSESVHOAWJC-UHFFFAOYSA-N 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 1
- 150000001504 aryl thiols Chemical class 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 525
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 115
- 239000012043 crude product Substances 0.000 description 107
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 106
- 239000007858 starting material Substances 0.000 description 98
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- 239000000243 solution Substances 0.000 description 86
- 238000000034 method Methods 0.000 description 77
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- DSFZYLCRXIWFFW-UHFFFAOYSA-N 2-[(2-carbonochloridoylphenyl)disulfanyl]benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(Cl)=O DSFZYLCRXIWFFW-UHFFFAOYSA-N 0.000 description 73
- SDNJNDFHCODQDQ-UHFFFAOYSA-N n-(2-ethylphenyl)-2-[[2-[(2-ethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=CC=C1CC SDNJNDFHCODQDQ-UHFFFAOYSA-N 0.000 description 72
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- 238000002360 preparation method Methods 0.000 description 34
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- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
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- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 1
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- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/69—Benzenesulfonamido-pyrimidines
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
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- C07D295/205—Radicals derived from carbonic acid
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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Oncology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cereal-Derived Products (AREA)
Applications Claiming Priority (2)
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US08/286,816 US5463122A (en) | 1994-08-05 | 1994-08-05 | Arylthio compounds |
US08/446,917 US5734081A (en) | 1994-08-05 | 1995-06-01 | Arylthio compounds |
Publications (1)
Publication Number | Publication Date |
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HUT77653A true HUT77653A (hu) | 1998-07-28 |
Family
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Family Applications (1)
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HU9700349A HUT77653A (hu) | 1994-08-05 | 1995-07-11 | Baktérium- és vírusellenes hatású N-szubsztituált 2-tio- és 2,2'-ditio-biszbenzamid- és -piridinkarboxamid-származékok és az ezeket tartalmazó gyógyszerkészítmények |
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US (3) | US5734081A (fi) |
EP (1) | EP0775110B1 (fi) |
JP (1) | JPH10504292A (fi) |
KR (1) | KR20040004371A (fi) |
AT (1) | ATE305923T1 (fi) |
AU (1) | AU710806B2 (fi) |
BG (1) | BG63301B1 (fi) |
CA (1) | CA2193845A1 (fi) |
CZ (1) | CZ26297A3 (fi) |
DE (1) | DE69534502D1 (fi) |
FI (1) | FI970417A (fi) |
HR (1) | HRP950429A2 (fi) |
HU (1) | HUT77653A (fi) |
IS (1) | IS1806B (fi) |
MX (1) | MX9700249A (fi) |
MY (1) | MY113732A (fi) |
NO (1) | NO308656B1 (fi) |
NZ (1) | NZ300073A (fi) |
OA (1) | OA10467A (fi) |
PL (1) | PL181425B1 (fi) |
RO (1) | RO119193B1 (fi) |
RU (1) | RU2156236C2 (fi) |
SK (1) | SK15497A3 (fi) |
SV (1) | SV1995000048A (fi) |
TW (1) | TW313565B (fi) |
UA (1) | UA52588C2 (fi) |
WO (1) | WO1996004242A1 (fi) |
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FR2736914B1 (fr) * | 1995-07-21 | 1997-08-22 | Adir | Nouveaux derives d'acide aminophenylphosphonique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
PL327135A1 (en) * | 1995-12-15 | 1998-11-23 | Warner Lambert Co | Method of obtaining [s-(r*, r*)]-3-methyl-2-(3-oxo-3h-benzo(d)isothiazol-2-yl)pentaic acid and [s-(r*, r*)], l-2{2-[2-(1-carboxy-2-methylbutylcarbamoyl)phenyldisulphonyl]-benzoylamino)-3-methylpentaic acid |
ZA974703B (en) * | 1996-05-30 | 1997-12-30 | Bayer Ag | Substituted sulfonylamino(thio)carbonyl compounds. |
WO1998040056A2 (en) * | 1997-03-13 | 1998-09-17 | Smithkline Beecham Plc | Pyrrolidine and thiazole derivatives with metallo-beta-lactamase inhibitory properties |
DE19735120A1 (de) * | 1997-08-13 | 1999-02-18 | Peter Hans Prof D Hofschneider | Verwendung von Thiolverbindungen zur Inaktivierung von Viren |
FR2779430B1 (fr) * | 1998-05-25 | 2001-07-13 | Pasteur Institut | Dithio-bis-nitrobenzenes substitues et leurs applications |
US6706729B1 (en) | 1998-06-19 | 2004-03-16 | The United States Of America As Represented By The Department Of Health And Human Services | Thiolesters and uses thereof |
DE69932820T4 (de) * | 1998-06-19 | 2008-06-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thiolester und ihre anwendungen |
UA74781C2 (en) * | 1999-04-02 | 2006-02-15 | Abbott Lab | Antiinflammatory and immumosuppressive compounds inhibiting cell adhesion |
EP1289945B1 (en) | 2000-05-19 | 2004-08-04 | Alcon Inc. | Aniline disulfide derivatives for treating allergic diseases |
PL365457A1 (en) | 2000-05-19 | 2005-01-10 | Alcon, Inc. | Disulfide derivatives useful for treating allergic diseases |
BR0110852A (pt) | 2000-05-19 | 2003-02-11 | Alcon Inc | Composições que contêm um derivado dissulfeto de benzamida para tratamento de doenças alérgicas |
WO2002056819A2 (en) * | 2000-12-21 | 2002-07-25 | Polymer Group Inc. | Absorbent articles with odor control |
WO2002055080A2 (en) * | 2001-01-10 | 2002-07-18 | Davide R Grassetti | Method of immunomodulation using thione-forming disulfides |
WO2002083126A1 (en) | 2001-04-11 | 2002-10-24 | Idenix (Cayman) Limited | Phenylindoles for the treatment of hiv |
US20040018983A1 (en) * | 2001-12-21 | 2004-01-29 | Achillion Pharmaceuticals, Inc. | Antifungal compositions |
US7101676B2 (en) * | 2002-01-11 | 2006-09-05 | Douglas Buechter | Methods for identifying compounds which inhibit binding of nucleocapsid 7 protein to HIV-1 RNA |
WO2004014364A1 (en) * | 2002-08-07 | 2004-02-19 | Idenix (Cayman) Limited | Substituted phenylindoles for the treatment of hiv |
NZ540799A (en) * | 2002-12-10 | 2008-09-26 | Virochem Pharma Inc | Compounds and methods for the treatment or prevention of flavivirus infections |
DE60329326D1 (de) | 2002-12-19 | 2009-10-29 | Vertex Pharma | Tace inhibitoren |
WO2004096147A2 (en) * | 2003-04-28 | 2004-11-11 | Idenix (Cayman) Limited | Oxo-pyrimidine compounds |
JP4771468B2 (ja) | 2003-12-26 | 2011-09-14 | 正敏 萩原 | Sr蛋白質のリン酸化制御方法、および、sr蛋白質の活性制御剤を有効成分とする抗ウイルス剤 |
AU2005305609B2 (en) | 2004-09-17 | 2011-10-06 | Idenix Pharmaceuticals, Inc. | Phosphoindoles as HIV inhibitors |
US20060185098A1 (en) * | 2004-12-03 | 2006-08-24 | Sylvain Kravtchenko | Composition for bleaching and simultaneously dyeing keratin fibers, comprising 7-(6'-methylphenylazo)-1-acetamido-3,6-disulfo-8-hydroxynaphthalene |
NZ575831A (en) | 2006-09-29 | 2011-12-22 | Idenix Pharmaceuticals Inc | Enantiomerically pure phosphoindoles as hiv inhibitors |
EP1911451A1 (en) * | 2006-10-10 | 2008-04-16 | INSERM (Institut National de la Santé et de la Recherche Medicale) | Protein-kinase CK2 inhibitors and their therapeutic applications |
JP2010509205A (ja) | 2006-11-07 | 2010-03-25 | プロテオロジクス リミテッド | Posh及びposh−ap阻害剤としてのピリミジン誘導体 |
US8618324B2 (en) * | 2007-03-13 | 2013-12-31 | Board Of Regents, The University Of Texas System | Composition and method for making oligo-benzamide compounds |
WO2011150360A1 (en) | 2010-05-28 | 2011-12-01 | The Board Of Regents Of The University Of Texas System | Oligo-benzamide compounds and their use |
WO2013078288A1 (en) | 2011-11-23 | 2013-05-30 | The Board Of Regents Of The University Of Texas System | Oligo-benzamide compounds for use in treating cancers |
WO2013078277A1 (en) | 2011-11-23 | 2013-05-30 | The Board Of Regents Of The University Of Texas System | Oligo-benzamide compounds and their use in treating cancers |
WO2017070084A1 (en) * | 2015-10-19 | 2017-04-27 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as nitroxyl donors |
JP6814312B1 (ja) * | 2020-02-05 | 2021-01-13 | 株式会社タイショーテクノス | 抗ウイルス剤及び物品に抗ウイルス性を付与する方法 |
CN111647034B (zh) * | 2020-05-13 | 2021-05-28 | 山东大学 | 2-巯基苯甲酰胺硫酯类化合物及其制备方法和应用 |
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DE724034C (de) * | 1938-11-04 | 1942-08-17 | Algemeene Kunstvezel Mij N V | Verfahren zum Erzeugen farbiger Glasfasern |
US3012039A (en) * | 1958-03-14 | 1961-12-05 | Ici Ltd | 2-p-chlorobenzyl-1, 2-benzisothiazolone |
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DE2602643C2 (de) * | 1976-01-24 | 1984-12-20 | Bayer Ag, 5090 Leverkusen | 1,2-Benzisothiazolinone-3, Verfahren zu ihrer Herstellung sowie Arzneimittel |
GB1560726A (en) * | 1976-04-28 | 1980-02-06 | Beecham Group Ltd | Isothiazolo-pyridines |
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DE3411385A1 (de) * | 1984-03-28 | 1985-10-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von o,o'-dithiobenzamiden |
US4975367A (en) * | 1986-04-04 | 1990-12-04 | Miles Inc. | Catalytic test composition intended to produce a range of colors |
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MX9205549A (es) * | 1991-09-30 | 1993-05-01 | Jess G Thoene | Metodo para el tratamiento de vih. |
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1995
- 1995-06-01 US US08/446,917 patent/US5734081A/en not_active Expired - Fee Related
- 1995-06-07 US US08/474,875 patent/US5668291A/en not_active Expired - Fee Related
- 1995-07-11 RU RU97103207/04A patent/RU2156236C2/ru not_active IP Right Cessation
- 1995-07-11 KR KR10-2003-7003049A patent/KR20040004371A/ko not_active Application Discontinuation
- 1995-07-11 PL PL95318540A patent/PL181425B1/pl not_active IP Right Cessation
- 1995-07-11 DE DE69534502T patent/DE69534502D1/de not_active Expired - Lifetime
- 1995-07-11 RO RO97-00227A patent/RO119193B1/ro unknown
- 1995-07-11 MX MX9700249A patent/MX9700249A/es unknown
- 1995-07-11 EP EP95926276A patent/EP0775110B1/en not_active Expired - Lifetime
- 1995-07-11 NZ NZ300073A patent/NZ300073A/xx unknown
- 1995-07-11 AU AU30087/95A patent/AU710806B2/en not_active Ceased
- 1995-07-11 JP JP8506523A patent/JPH10504292A/ja not_active Abandoned
- 1995-07-11 WO PCT/US1995/008802 patent/WO1996004242A1/en not_active Application Discontinuation
- 1995-07-11 AT AT95926276T patent/ATE305923T1/de not_active IP Right Cessation
- 1995-07-11 CZ CZ97262A patent/CZ26297A3/cs unknown
- 1995-07-11 SK SK154-97A patent/SK15497A3/sk unknown
- 1995-07-11 HU HU9700349A patent/HUT77653A/hu unknown
- 1995-07-11 CA CA002193845A patent/CA2193845A1/en not_active Abandoned
- 1995-07-25 TW TW084107669A patent/TW313565B/zh active
- 1995-07-26 HR HR08/446,917A patent/HRP950429A2/hr not_active Application Discontinuation
- 1995-08-04 MY MYPI95002289A patent/MY113732A/en unknown
- 1995-08-07 SV SV1995000048A patent/SV1995000048A/es unknown
- 1995-11-07 UA UA97020486A patent/UA52588C2/uk unknown
-
1996
- 1996-12-13 OA OA60937A patent/OA10467A/en unknown
-
1997
- 1997-01-31 FI FI970417A patent/FI970417A/fi not_active IP Right Cessation
- 1997-02-03 IS IS4425A patent/IS1806B/is unknown
- 1997-02-04 NO NO970495A patent/NO308656B1/no not_active IP Right Cessation
- 1997-02-04 BG BG101189A patent/BG63301B1/bg unknown
- 1997-05-15 US US08/857,116 patent/US5929114A/en not_active Expired - Fee Related
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